Hard On the Trail Ch. 05

I drove Daddy to the trail that morning. It felt weird having him in my car. The only place I'd ever had him quite so personal was in me and in my bed. In fact that was what made our relationship so awesome. He came when he wanted to cum, he fucked my brains out and then he was gone. There was no sloppy emotional junk getting in the way.

I parked the car and we hopped out. Daddy looked pretty proud of himself, I wondered why. He looked anxious and excited. I didn't know if this was normal or some sort of rite of passage. He stretched and said, "I hope your bitch is on the trails today. I've been watching this one for weeks! He's exactly what you need!"

How did he know what I needed? How did he know this guy was it?

Daddy went ahead of me on the trails, we ran for about 20 minutes before suddenly he nodded at someone running in the opposite direction. I turned to check him out as he passed and saw he looked over his shoulder at us and then nervously back ahead. I almost ran straight into Daddy who was turning on his heel to follow after the man. Was this him? Was this supposed to be my bitch?! And he could tell just from that? How? As if to answer my question Daddy breathlessly explained, "did you notice, he looked back at us? He's curious! He wants your dick, he just doesn't know it yet. It's all in the mind you see. You'll learn!" And with that we were off.

The man ahead of us kept looking over his shoulder at us. He'd slow down, we'd slow down, he'd speed up, we'd speed up. Up ahead I saw the trail I'd made my escape on a long time ago. I wondered...he wouldn't...would he? Sure enough, as we approached he made a bit of a turn into the center of the trail and then was off down that secluded pathway into the woods. I slowed to a halt stunned. This was how my fate had been sealed. My stomach was both excited and sickened. This man had just unknowingly given Daddy the sign for fucking his ass. I watched, expecting to see Daddy pursue him. He didn't. He stopped at the opening to the pathway and looked at me. "What are you waiting for? Go get him?"

"What? are you out of your mind?"

"You're ready, just go up there and make him your bitch!"

"Okay, first of all, let's pretend he ACTUALLY wants me to fuck him --"

"He does"

"Okay, let's pretend we know that for sure, I've never done this before, how the hell am I supposed to go up to a complete stranger and plow their ass."

Daddy started laughing, "listen boy, just go up there and if you are lost for ideas, do to him exactly what I did to you. You'll get your own style, I know you will, but for now you better hurry before he thinks you're not interested."

"you're fucking crazy, what if he attacks me? What if he runs back this way and calls the cops?"

"he won't, but if he does, it was a simple misunderstanding. Everyone knows that's where we guys go to get our rocks off, the cops will be hard pressed to believe he didn't go up there for the same reason and have some sort of anti-gay remorse."

Everyone knew that was where guys went to fuck? I hadn't known that. I was willing to bet that this guy didn't know that either. But Daddy was looking impatient and I knew the guy would be WAY up the trail by now so I started up the path into the woods just as I had months before.

It took a few moments but I eventually caught up to him. I didn't want to spook him so I kept a slight distance. But even at my distance I could see a trail of sweat lining the crack of his ass on his shorts. My cock started to harden and slap against my thigh. He wasn't that old, probably about my age. I'd never been with anyone besides Daddy this way. Now I was supposed to dominate someone my age?

The path began to narrow and become more difficult, I saw the man slow his pace and the anticipation began to rise. This was it, this was the moment. As he stopped and reached up for his headphones to pull them out of his ears, I came to a stop behind him. I could smell his musk and I just wanted to bite into his shoulder while he screamed out in ecstasy! That's when I froze, how do I get from two strangers standing in the woods to two strangers fucking in the woods? I thought to what Daddy said, "If you get lost for ideas, just do what I did." I reached forward with my hand, trembling slightly I took two fingers and traced them down the sweat stained crack of his ass. So firm, so enticing.

Just as I expected he jumped around and back away from me and screamed. "What the hell are you doing?! Fucking queer!"

I was shaking inside but I tried to remain firm, I had to own this! "Hey now, is that any way to talk to your Daddy?!"

"You fucked up shit! Go back the way you came."

"Oh I'm not going anywhere! You're the one who had me up to fuck central."

"Fuck central?! What the hell are you talking about?!"

"Everyone knows this is where guys go to have a good time. Don't pretend to be so innocent. Unless it's what turns you on!" I stepped forward as I spoke and reached to drag my finger down his chest. So hard and warm. My cock flexed, oh it was ready, but was he?!

I was losing him, I had to think fast, what would Daddy do? "HEY! You had me run all the way up here for a piece of ass you little cock tease. Now I'm getting my piece of ass whether you give it to me or I have to take it! Now the question is, do you want to do it out here in the open where someone could walk in on us or would you rather pick a quiet spot where we can be alone?"

For some reason that seemed to work. Even though I had no way of holding him physically, he seemed to be mentally in a choke hold. It didn't make sense to me but I guess my tone expressed my commitment to taking his ass. His head dropped and he began to turn towards the deeper woods. But not before I first noticed his cock. Holy shit, he was half-mast! Daddy was right, he was into this! Just like I had been. I hadn't known it at the time and this guy didn't know it yet either. But when I was done with him he'd be begging for more!

He lead me off into the woods, we passed by the rock where Daddy had taken me, where I'd christened the ground with my cum. The site of that rock made me so hard I wanted to flop this kid down right there and just take him. Listen to me, this "kid" he was my age, shit it was fun getting into this role!

He didn't take me far, stopping near a small huddle of trees he stopped. I looked over my shoulder, perfect, I could see my rock from here, I should position us so that I could look at it while I took him. Help keep me into character, just reliving the moment myself and executing it as planned.

"What now, ass hole?"

I snapped back into the moment, "Don't talk to your Daddy that way, you call me Daddy or you call me Sir! You got it?!"

"Yes sir!" he growled back.

"Good, now take off your pants kid...fuck it, take everything off.

He stepped behind a tree, how fucking innocent, as if I wasn't going to be violating him in the most intimate of fashions in a few moments. His shorts fell out from behind the tree and commonsense kicked in. His wallet...I needed his id for this to work just as it had with me! I grabbed his shorts fast, pulled out the wallet and shoved his id in my wallet. Discarded the whole package quickly back where it had been. Just in time as he stepped around the tree completely naked except his running shoes. Damn! His cock was so hard! "Mmm nice dick!"

"Shut up!"

I reached out and touched it. He flinched at first and then moaned a bit as I stroked it.

"I'm not gay you ass hole!"

I shoved him down and sat on his chest, "What did I tell you to call me?! Do you WANT me to remind you?!"

"Sorry! Sir!"

I stood back up to adjust myself and he sat up. "Get up, kid." he did as he was told. "Go over to that tree!" He dragged his feet but he was very obedient, holy shit...he was eating out of the palm of my hand. I made a mental note to thank Daddy later. "Good, now put your hands on the tree and bend down really far so your ass sticks out."

He rolled his eyes but did as he was asked, that's when I came over sucking on my fingers as I approached. When I reached him I put one hand on his lower back causing him to flinch, the other with my wet fingers reached for his pink virgin hole. As soon as I touched it he jumped up and said, "Nu uh! I can't do this! I'm not gay, sir!"

I laughed, "I'm not gay either. This isn't about being gay, this is about knowing what you need. I'm a guy, I know what you need. I can make this feel so good for you if you'll just stay still."

"And what if I don't?"

"If you don't then this will hurt like nothing you've ever felt before, but either way I'm going to fuck you before this is done and it's just a matter of how much pain you're going to feel. Now put your hands back on that tree, stick your pretty little ass out to me and behave."

He did as he was told. I re-lubed my fingers and this time he behaved. I slowly slid one at a time into his ass and once in just let them sit there for a while. Let him get used to the feeling of being slightly full. After a while I spit on his ass which made him groan and let the spit drip onto my fingers as I pulled them out and then shoved them back in. Now, to find that spot. I began slowly pumping my finger as he groaned into the tree bark. I wiggled them as I moved them, reaching for a soft spot that would cause a reaction in him. I was just about to give up when suddenly a soft, "ahhh" escaped his mouth. I grinned ear to ear, that must be it. I flicked my fingers across it a few times and then, like magic, he reached under his belly and began stroking his dick. I don't know that he even realized it yet. I moved a little faster now and he really began to respond, "oh yes, oh yes...mmmmm yes." Alright, he was ready, now to shove my dick in him! Fortunately for him I had come with lube. I wasn't a huge fan of spit, although in a bind it worked, but lube was sooooo much better.

I pulled my fingers out and stood to prepare my cock. When my fingers left he moaned that familiar disappointed moan I always gave. He wiggled his ass begging me to put them back, while he stroked his dick. I reached into my pocket, pulled my tube out and then with my other hand I pulled my dick out of the two flaps in my boxers and shorts. My continued absence from his ass caused him to look over his shoulder to see what was up. When he saw my big dick out he started to stand up, "Oh no!" He hollered, "There ain't no way I'm letting you stick your dick in my ass! I'm not some queer!" I pounced on him with all of my body, dropping my lube in the process.

"I already told you, this isn't about being gay it's about sex, pleasure. And I warned you, either you give it to me or I'll take it. So what's it going to be?"

He squirmed under me, giving me my answer. What was I to do? I had to follow through or I'd lose him and I was so hot now I needed this ass! I looked down at his pucker as he squirmed, it was still dripping with my spit from earlier, that should be enough. It'd hurt him for sure though.

"Alright," I said as he continued to squirm under me, "I warned you. I could do this nice and we'd both get off with little to no pain. But you had to be a little bastard and now I am just going to have take what is mine dry!" And with that my dick was pressed up against his ass hole.

"NOOO! NOOO!" he squirmed harder.

"Oh yes, you little shit. Hold on tight cause it's going in!" And I began to push against his opening. Even with my two fingers having been in there earlier it was as though nothing had ever opened this ass. But I was bound to take what I earned. I shoved as hard as I could until I popped inside. I was shocked by how much it hurt ME. But the sounds coming out of him pushed me forward, literally.

My dick felt like a hundred tiny razors were pulling back but the intense response I was getting from him pushed me forward. I put both hands firmly on his shoulder blades, pushing him down into the dirt and I started to pound into him. With each thrust I would utter a word as I degraded him just as I had been degraded, "I ... TOLD... YOU...NOT...TO...FIGHT!" the pain...it was slowly subsiding with the addition of precum, but it still burned. I continued a steady thrust, "Now, are you going to stop fighting like a little bitch and take what Daddy brought you or are you going to continue to wrestle me and force me to take you like this?"

He stopped squirming and I could tell he was sobbing. "Please, take it out. Don't fuck me. I have money, you can have all my money. But please, don't fuck me!"

I slowed my thrusts making them deep and hard, "I don't want your money. I want your ass. I want to make you cum. I want to make this feel good for both of us. But you had to go and be a little bitch about it. Are you going to behave now?"

He nodded, "yes sir!"

"Alright, this is going to hurt coming out but if you keep still I'll lube it up and it'll feel amazing going back in! Understand?"

He nodded. I began to pull my dick out. Holy shit the vacuum of his ass pulling on my dry cock was almost too much pain for me to handle. He screamed out some more as I finished pulling out and he whimpered into the ground. Something about "please god, make this stop." and stupid mumbling about, "just get it over with." What a baby!

Once out I reached for my lube and lathered myself and his pucker up. "alright, are you ready."

He was still sobbing, "Yes sir" he choked.

"Alright, now stay still while Daddy starts up, I'll go slow and I'll find your button again." And with that I slowly reentered his ass. This time it felt slick and tight. Nothing like Daddy's. His ass was not used, it was virginal. He was my little virgin. I lost control for a moment at that idea and began to pump him a little harder. Fortunately the size of my cock being much bigger than my fingers also meant I hit his button a lot sooner. He was under me moaning and rubbing his dick again.

"Oh yeah...yeah...fuck yeah...right there."

This was it, he was loving it, Daddy was right...he was my little cum slut. I didn't have to worry any more as I saw him biting his lip and stroking his member. I got excited. I grabbed his shoulders and pushed him up against the tree. While doing this I noticed a figure watching us. "Oh shit" I thought, "Was it a cop?" I then noticed the movement the figure was making. They were jerking off...I squinted, it was Daddy. He was watching from the bushes. Watching his cum slut become a man. I had an audience that I wanted to impress and with that, all bets were off. I turned us around the tree so my back was to Daddy. I lowered my shorts off my backside, just enough so that it didn't effect my cock pounding into this sluts ass but enough to let daddy get a good view. I slid the kid down the tree trunk so could bend more as I fucked him and reached behind me to play with my ass while I did it. I heard a moan from the bushes and knew I had him completely warped. My cock flexed bringing me back to the man moaning underneath me. I left my shorts down to temp Daddy but replaced my hand back on my bitch's hips.

"Yes, oh god yes, fuck, I'm going to cum."

Holy shit, I was going to make him cum...I was going to cum... this was fucking amazing! I began to bring the focus in, "Yeah, you like that, you like my dick in your ass you little cum slut?"

"Yes, sir! Fuck my ass, sir!"

"Yeah, fuck your tiny little ass. Fucking make you cum and then I'm going to pound your ass until I fill you."

"Yes, sir, I want you to fill my ass!"

"Yeah, want me to fill your ass, are you my dirty little anal slut? Huh? Want me to FUCK you" and I slammed him harder into the tree.

"Oh...ohhhh yes ohhhh right there...fuck... arrroooogggggg" I felt his ass tremble and flex around my cock as his cum sprayed the tree in front of us. It got me so hot I knew it wouldn't be long for me. I shoved him down so his face was right in front of his cum and his ass was prime. I grabbed onto his hips with both hands and began to plow his ass, "Fuck yea, make Daddy cum. You fucking cum slut. I'm going to fill your ass and then you'll be my bitch forever!"

His ass tightened and he straightened up, "WHAT?! That wasn't part of the deal!"

I'd gotten carried away and triggered the same response Daddy had triggered in me. I was too close to give a shit. He'd enjoyed himself, it was my turn now. I shoved him down further, I wanted him to be my cum bucket, just like I was for Daddy.

I felt all my primal urges come to the surface and I pounded deeper into him than I had before. He began to moan out in pain, he'd already cum, all that was left for him was pain. Sweet, merciful pain. Harder, faster, deeper I plowed into him. Grunting and growling like a bear until finally I felt my seed spurt out. It pooled into his ass as I groaned and leaned forward. I was almost sitting on him as I finished. Pouring my cum deep into his ass.

The sweat beading into my face as I leaned over him. He was still panting and his cum dripped from the trunk towards the ground. I stood up and slowly retrieved my cock. He moved as if he'd stand and I slapped his ass to make him wait.

I reached his anus with my fingers, pulled it open and saw my cum sitting there in his anal cavity. I began pulling and pushing my ass together and apart and watched as my cum emptied into his bowels. When I was satisfied at it's depth I slapped his ass and let him go.

Hurriedly he got on his shorts and shirt, took a look over his shoulder at me, blushed and then ran off. I touched my ass pocket where my wallet held his address. Would I use it?

I didn't really have long to think about it as I felt Daddy's hand on the back of my shorts. He yanked them down, pushed me forward and within seconds I felt the head of his cock pushed up against my ass hole.